Mr. Stillman's Opus

If you're only using your Health Savings Account (HSA) to pay for co-pays and prescriptions today, you’re missing out on its biggest superpower. In this episode, John reveals how to “hack” your HSA and turn it into a tax-free retirement goldmine. He also shares tips on contribution strategy, the portability of HSAs, what qualifies as a medical expense, and how to retroactively reimburse yourself in retirement.

Here’s what we discus...

Bees might not seem like financial gurus, but when it comes to patience, long-term planning, and compound growth, they might just outsmart most investors. In this episode, John teaches on what his personal beekeeping hobby taught him about investing, and why the early years of building wealth often feel frustrating or futile.

Here’s what we discuss in this episode:

🕰️ Why early returns often look discouraging

💸 Feeling behind? Fo...

A new tax proposal, referred to as “The Big Beautiful Bill,” has officially passed the House. But before anything’s set in stone, it has to make it through the Senate, where revisions are all but guaranteed. The bill’s main goal? To extend several provisions of the 2018 tax code, with a few adjustments and updates along the way. In this episode, John breaks down what’s currently in the bill, what might shift in the Senate, and how ...

For a lot of folks, retirement and travel go hand-in-hand, whether that’s taking a trip to Europe or rolling into every Cracker Barrel in the Southeast. But here’s the thing: dreaming is free, but the travel costs aren’t. In this episode, John shares how to build a realistic, flexible plan that supports your travel goals in retirement, whether it’s an RV road trip to national parks or annual international adventures with a passport...

When the market takes a dive, most people panic. But the most successful investors often see downturns differently. Being able to recognize opportunity in the middle of market uncertainty can help you make critical decisions during difficult market environments. Let’s talk about what steps you can take to strengthen your plan while others sit on the sidelines.

We'll cover four smart strategies that can work during volatile periods,...

Tax season is here, but did you know that filing your 2024 return is only part of the equation? With the 2025 tax changes in place, John breaks down key areas where you may be able to reduce your tax bill. With increased standard deductions and higher retirement contribution limits, now is the time to evaluate how you can plan smarter and potentially put more money toward your future.

In this episode, we dive into the major tax cha...

Once you’re on a fixed income in retirement, it can be difficult to open the checkbook to pay for major expenses. Emotion and logic both play into the decision, and many spouses can feel apprehensive about spending large sums of money without a paycheck still coming in. So how do you determine if you can afford that home renovation you’ve always wanted and what’s the best way to convince your partner it’s going to be okay long-term...

There’s a lot of anxiety out ​there ​right ​now ​about ​the ​market ​and ​the ​current ​economy ​that ​we're ​experiencing. ​People are concerned about the uncertainty surrounding Social Security, DOGE, tariffs, and more. So ​I ​wanted ​to ​get ​on ​here ​and ​try to ​dispel some of the ​myths, ​talk ​about ​what's ​actually ​happening, ​and ​then ​drill ​down ​specifically ​to ​what ​you ​should ​be ​doing ​yourself.

Here’s some o...

What’s the average age that people retire? While that question can give you an idea of what most Americans do, it’s best to understand why people choose the specific ages they do. This video will explain the key ages that influence retirement decisions to help you identify the factors that might affect your timeline.

We’ll tell you why the milestone ages begin at 59.5 and what ages are most important for Social Security and Medicar...

What happens when you get remarried and want to create a new will and estate plan with your new spouse? Do you have to change all of your previous beneficiaries or will the new will override those existing designations? That’s the question we’re answering in this week's show. 

Here’s what we discuss in this episode:

0:00 – Intro

0:51 – Beneficiaries override the will

2:32 – Estate planning challenges with second marriages

Conne...

With Halloween on the horizon, we’re rolling out a themed edition of the show today by tackling some of the trick or treat decisions of the financial planning world. We’re going to present John with four different products that have risen in popularity recently and find out whether he would characterize them as tricks or treats.

Here’s what we discuss in this episode:

0:00 – Intro

1:20 – Home equity line of credit

5:18 – Infinite...

Getting laid off or forced into retirement earlier than expected can be a big blow emotionally and financially, but it’s a life event that many people will have to navigate. If you find yourself in this position of no longer having a job before you were prepared to retire, should you go find another job or can you find a way to retire without it?

Today we’re answering a question we received recently from someone who is 61 and tryin...

Social Security timing is one of the most crucial decisions you’ll make in your retirement planning journey. Should you wait until 70 to claim your benefits, or is it better to start earlier?

Today we’re going to answer a question from someone who planned to wait until 70 for Social Security so they didn’t leave money on the table, but now that they’re approaching age 68, they’re having second thoughts about waiting. So what’s the ...

As we age, one of the most pressing questions we face is how to manage long-term care expenses. What coverage will you need and what’s the best way to pay for that coverage? Today we answer a question about purchasing LTC insurance and whether it’s worth doing while you’re in your 50s.

John will discuss whether it is a necessary investment for those nearing retirement age and examine alternative options such as self-insuring and le...

It can be challenging for a lot of folks to think about legacy planning because it takes a lot of forward thinking. Not everyone wants to plan that far ahead, but for some, it’s incredibly important to leave their loved ones with an inheritance.

Today we are answering a question from someone who wants to leave money for their children and grandchildren but also wants to ensure that they’re not paying more in taxes on that money t...

Instilling good financial habits in children starts at a young age, but that doesn’t mean that every lesson will stick in adulthood. Once your kids start working and earning significant money for the first time, it’s pretty common to put spending ahead of saving. As parents, we want to help them establish good financial habits but what’s the best approach to do that?

In this video, John will address a question we received from a pa...

With college costs continuing to rise, some grandparents wonder if there’s anything they can do to help ease the burden of college expenses for their grandchildren. Today we’ll explore the best strategies for those who want to support their grandchildren’s college education without compromising their own financial stability.

The 529 plan gets most of the attention when it comes to college savings, but we’ll share a few more optio...

It’s not uncommon for children to stay on their parent’s payroll in some capacity when they’re adults, but that could end up impacting the parent’s ability to retire. At what point do you move your kids off of the payroll and what’s the best way to handle that conversation?

In this episode, we’re going to address this situation and talk about how it ends up happening for parents. John sheds light on this issue, sharing his own expe...

When you have multiple IRAs, managing them across different platforms and figuring out your RMDs for each account can be a little bit tricky. So what’s the best way to manage these accounts? Should you consider consolidating your IRAs?

Today’s featured question comes from a comment left on one of our previous videos so thank you for the contribution. Here is the question John will answer:

We have multiple IRAs set up over the years...